4-(Dimethylamino)cyclohexan-1-one--hydrogen chloride (1/1) → HCID 12891865, compound

HRID 128136Notes

Reaction equation

HRID 128136 reaction equation
Cl.C(OC1C=C(NN)C=CC=1)C1C=CC=CC=1.Cl.CN(C)C1CCC(=O)CC1.Cl.[CH3:30][N:31]([CH3:53])[CH:32]1[CH2:44][C:43]2[C:42]3[C:37](=[CH:38][C:39]([O:45][CH2:46][C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)=[CH:40][CH:41]=3)[NH:36][C:35]=2[CH2:34][CH2:33]1.Cl.CN(C)C1CC2C3C(=CC=CC=3OCC3C=CC=CC=3)NC=2CC1>O>[CH3:53][N:31]([CH3:30])[CH:32]1[CH2:44][C:43]2[C:38]3[C:37](=[CH:42][CH:41]=[CH:40][C:39]=3[O:45][CH2:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[NH:36][C:35]=2[CH2:34][CH2:33]1

Participants

6

Reactant 4

HCID 127174484-(Dimethylamino)cyclohexan-1-one--hydrogen chloride (1/1)HCID 12891839(3-(Benzyloxy)phenyl)hydrazine hydrochlorideHCID 23470234HCID 23470234, compoundHCID 23470481HCID 23470481, compound

Product 1

HCID 12891865HCID 12891865, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3-benzyloxyphenylhydrazine hydrochloride (140 g.) and 4-dimethylaminocyclohexanone hydrochloride (100 g.) in 3 liters of ethyl alochol was refluxed for six hours and evaporated to dryness. The solid was suspended in 1 liter of water and filtered to give 119 g. of 3-(dimethylamino)-7-(benzyloxy)-1,2,3,4-tetrahydrocarbazole hydrochloride (Example 239). The water filtrate deposited a solid which was recrystallized from ethyl alcohol to give 38 g. of 3-(dimethylamino)-5-(benzyloxy)-1,2,3,4-tetrahydrocarbazole hydrochloride, m.p. 207°-209° C.

Workup

  1. customevaporated to dryness
  2. filtrationfiltered
  3. customto give 119 g
  4. customwas recrystallized from ethyl alcohol
  5. customto give 38 g

Sources & evidence

ORD record
ord-2ae54193e1e94db0bcc272249d7e09bb
Source dataset
uspto-grants-1981_03
Patent number
US04257952

Reaction notes

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